RORY: I’m just saying I’m no stranger to the Big Apple.
JESS: You are if you’re calling it the Big Apple.
The Big Apple is a nickname for New York City, first popularised in the 1920s by John FitzGerald, a sports writer for The New York Morning Telegraph. Its popularity since the 1970s is mostly due to a promotional campaign by the city’s tourism authorities to boost the city during a fiscal crisis.
Although Rory says she’s been to New York a few times, she only mentions The Bangles concert in 2001 and a 2000 shopping trip where she didn’t even get out of the car. This could very well be her third trip to New York (and the second where her feet touched the ground!).